


Dean Winchester imagines

by fallingofftheaxis



Category: Supernatural
Genre: M/M
Language: English
Status: In-Progress
Published: 2019-01-16
Updated: 2019-06-29
Packaged: 2019-10-11 10:04:28
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 1,319
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17444810
Author URL: https://archiveofourown.org/users/fallingofftheaxis/pseuds/fallingofftheaxis
Summary: A collection of Dean Winchester imagines from my blogs





	1. Dean and his Fucket list (nsfw)

Dean has had lots of sex in lots of different ways but when you started dating and brought up the idea of a fucket list, he was all for it.

He had a fairly long list but over time he was able to cross them off one by one.

6\. In the back of the Impala

This was the first one crossed off the list and just a few days after he made it. Sam was busy doing research in the library and you two were bored waiting in the car for him. When Sam returned the windows were fogged, Dean’s hair was a mess and the backseat smelled like sex. Sam refused to get in the car and insisted he would walk back to the motel room.

34\. In a bar bathroom

You and Dean went out for drinks after successfully ridding a home of its poltergeist. You played pool, you took shots and ended up making out against the jukebox. By the end of the night he had you holding onto the sink counter in the men’s bathroom so tight your knuckles turned white as he fucked you from behind.

15\. With Sam still in the room

This one wasn’t as wild as the others. Sam was asleep in the bed next to you guys and Dean took this as an opportunity to jerk you off. You knew you would be testing your limits if you tried anything else because of how squeaky the bed was but Dean still counted the act and checked it off the list.

27\. The mile high club

Dean hates flying and this particular excursion was a reach even for him. The only reason it happened was because the Impala was out of commision and Ellen had an emergency back in Montana. You convinced Dean to get on a plane solely with the promise of sex in the bathroom to get another escapade off his list.

12\. Edging

This one turned out to be Dean’s favorite. He knew about edging of course but never had the patience to try it. He was used to one night stands and getting in as many orgasms as he could but now that he was in a relationship with you and it was something he would finally get to try. Four times you brought him so close to his release before pulling away. As desperate as he was to get off it was one of the best sexual experiences he ever had.

3\. Handcuffs

As simplistic as it was Dean was very excited to try this with you. He insisted on using real metal handcuffs ‘cause he liked the extra sting it gave him on his wrists. He nearly tore the headboard right off the motel bed with how hard he was pulling on the cuffs while you fucked him. Sam however was not as happy when you couldn’t find the key and he had to pick the lock open of the handcuffs on his very naked brother.

21\. Sex tape

Dean had plenty of nude photos of himself as well as the ones you’ve sent him on his phone but he was intrigued by the idea of actually filming you two having sex. He set his phone propped up on the dresser at an angle that could get the full view of the bed. Now when he needs something to get him off quickly he pulls the video out and jerks off to the sight of him fucking you.

9\. Threesome

Dean didn’t think you would go for this one but you guys met a very atttactive man at a bar and you had had enough drinks to say what the hell and went back to his place. Dean’s grin was so big when he got to take this number off the list and later when you told him you’d be open doing it again sometime, he got a boner right then and there.

43\. With food

The one thing Dean loves as much as sex is food. You started the night with him feeding you chocolate covered strawberries accompanied by champagne and moved onto the whip cream. You sprayed and licked whip cream off all over his body. His neck, his chest, his nipples, his abs, his thighs and finally off where he wanted you most. This would surely not be a one time thing.

Dean kept this list in the inner pocket of his leather jacket, happily adding to it whenever he thought of something new. Sam once put Dean’s jacket on by mistake and found the list. He couldn’t look at either of you in the eyes for weeks but Dean didn’t care. He was damn proud of his fucket list.


	2. Two birds one stone

“So I’m finally gonna get to meet this new boyfriend of yours,” Sam said placing the coffees you two ordered on the table.

“I can’t wait for my boyfriend and my best friend to meet, i think you guys are really gonna get along,” you smiled taking a sip of your coffee.

“What was his name again?”

“Dean Powell,” you told Sam.

“Funny my brother’s name is Dean too,” Sam laughed.

“Oh yeah you have to bring your brother around sometime I’d love to meet him.”

“Eventually, Dean and I haven’t seen each other in a while,” he shrugged.

“I feel like i barely to get to see my Dean either, he’s always going out of town to see his dad-”

“Y/N, Sammy!” You heard the voice of you boyfriend call out.

“Dean,” you smiled as he leaned down to kiss you chastely, “wait, you already know Sam?”

“Dean?” Sam said surprised.

“Hey little brother,” Dean said patting Sam on the back.

“Okay what’s going on here?” You said confused.

“So Y/N i should tell you Powell isn’t really my last name, it’s Winchester and Sammy here is my baby brother,” Dean explained taking a seat at the table .

“Why did you use a fake last name?”

“I didn’t want it to be weird that i was dating my brother’s best friend… I also never exactly told Sam i was into dudes too” Dean shrugged.

“Mission accomplished,” Sam said shaking his head, “and by the way i akways knew you were bi.”

“So why tell us now?” You asked still trying to figure everything out.

“I had to come to get Sam anyways, figured i should just kill two birds with one stone,” Dean responded.

“Come get me for what?” Sam replied.

“Dad’s gone on a hunting trip and he hasn’t been home for a few days.”


	3. Snowed in headcanons (nsfw)

· you were in New York hunting with Sam and Dean in the winter

· you and Dean were supposed to meet up with Sam at the town library when you heard on the radio that the roads were closed because of the snow

· instead you two went to watching tv and eating whatever gas station food you had lying around

· then Dean looked at you with his hand on your thigh

· “we’re gonna be here a while so… You want to have sex?”

· you got on top of Dean and started making out

· it didn’t take long for both of you to get naked

· you were giving Dean a blowjob when his phone rang

· “where are you guys?”

· “sorry Sammy roads are- the roads are closed”

· “are you okay Dean?”

· “just fine gotta go”

· when Dean finally ended up fucking you the bed kept hitting the wall

· your neighbors kept banging on the wall from the other side to get you to stop

· but you didn’t

· Dean loves fucking you with you in his lap

· two hours later when Sam was finally able to get back to the room he found your clothes scattered around the floor

· he went into the bathroom and you guys were in the shower together

· “seriously guys? You couldn’t keep it in your pants while i was gone?”


End file.
